Start of Something New
by MadLuvBabe
Summary: Gabriella decides that she's ready for her first time with Troy. One-Shot. ***Sexual Content*** Updated! I've changed a few things and fixed some issues that were bugging me.


Gabriella rolled over and looked at her clock. _3:36. Ugh!_ Not that she had anything to do tomorrow, really. But if she fell asleep late, she would wake up late, and it would mess with her carefully tailored sleep schedule. She flipped onto her back and stared at the ceiling. It wasn't as if she wasn't tired. The Wildcats had won the state championship last night, and they had stayed at Troy's house until past one, partying it up. She had been exhausted when she got home, but now she was wide awake.

 _Troy..._ She absently played with the "T" necklace that pooled at the base of her throat. She reached for her phone on her bedside table. _Maybe he's still awake too..._ But she hesitated. She didn't want to wake him up, and if he knew she couldn't sleep, he would stay on the phone with her, no matter how tired he was. She smiled to herself. She truly had the best boyfriend ever. She rolled over again, determined not to bother him. She scrunched her eyes shut and tried to count backwards from one hundred. But she had just gotten to sixty three when she heard a tapping noise at the doors to her balcony. She ignored it. Sometimes the branches of the big tree out there got blown towards the doors by the wind.

 _Sixty-two...sixty-one...sixty..._ She jumped as the tapping came again, louder this time. Her eyes opened and she stifled a scream.

 _Someone is out on the balcony!_

She could see the silhouette of a person in the moonlight against her curtains. Her heart pounded and she sat up, reaching for her phone. Would they hear if she called nine-one-one? Would they hear if she ran from the room?

 _Maybe they'll go away if I scream._ Gabriella thought. She clutched her blankets and took a deep breath, preparing to let out a bloodcurdling scream.

 _Tap-tap-tap._ "Gaby? You awake?" The voice was barely louder than a hiss, but Gabriella would know that voice anywhere. She heaved a sigh of relief, adrenaline still pumping through her veins and scrambled out of the bed. She pulled back the curtains to check before flinging open the door.

And there he was. Still in the grey v-neck and jeans he had worn to the party, he grinned down at her, his hair a tousled mess on top of his head.

"Hey." He said anticlimactically. A wave of irritation hit Gabriella and she smacked his chest. He recoiled in surprise, and her hand stung from the contact with his hard pectoral muscles.

" _Hey?_ You nearly gave me a heart attack, Troy Bolton! What the hell are you doing here?"

He shrugged, his grin slightly more wary. "I couldn't sleep, so I thought I'd see if you were up."

Gabriella rolled her eyes. "Haven't you heard of a phone?"

"Yeah, but if you were asleep, I didn't want to wake you up. I figured if I knocked gently, and you were asleep, you wouldn't hear it and I'd leave." He shrugged again as if this made perfect sense. Gabriella narrowed her eyes.

"How did you get here?"

"Walked."

"You walked? That's like a half hour's walk, at least?" He crammed his hands into the pockets of his jeans and flipped his hair out of his gorgeous blue eyes.

"No big deal. Besides, if I had taken the truck, it would have woken my parents up. The muffler is gone to shit." Gabriella suppressed a giggle. There was always something wrong with Troy's truck. She noticed his eyes travelling down her body and she remembered, for the first time, the lacy, cranberry coloured teddy and matching panties that she had worn to bed. Her mother had bought them for her, telling her that she was becoming a lady, and needed to stop wearing old sweats to bed. Surprisingly enough the quasi-lingerie was quite comfortable and made her feel pretty. But as the wind caused the hem to dance around the tops of her thighs, she remembered how short the little teddy was, not to mention practically see through. She hoped Troy couldn't see anything in the moonlight, but she crossed her arms over her chest anyway.

Troy blushed and forced his eyes back to her face. He didn't want to make her feel self conscious. She had a gorgeous body, of course. _Damn near perfect...and that little outfit..._ his cock throbbed pre-emptively, beginning to press against his jeans. He pushed his hands further into his pockets, hoping to mask the bulge. _Come on, Bolton, get a grip._

"Well..." Gabriella tucked her thick, curly brown hair behind her ear as the wind tried to toss it across her face. "Since you're here, and I _am_ awake, why don't you come in for a bit?"

Troy tried not to grin too widely as he followed his girlfriend back into her dark room, closing the balcony door behind him. Gabriella went over to her bedside table and turned on her little lamp, bathing the room in a very gentle, warm glow. Then she went over to her bedroom door and locked it. She was blushing when she turned back to Troy.

"My mother sleeps like the dead, but you can never be too careful." She explained, getting nervous for some reason. "She'd throw you off the balcony if she found you here."

Troy nodded, still standing in the middle of the room. The nervousness in the space between them was palpable. Troy had been in Gabriella's room a million times, but never so late. He had never seen her pyjamas before... _seriously, that's what she sleeps in?_ She looked even more gorgeous than usual, the cranberry colour playing against her tanned skin and dark hair, the hem of the little top hitting her upper thighs, the v-neck plunging down between her pert chest...Troy forced his gaze down to the floor as he jeans became even tighter. He wished he was wearing sweatpants.

Gabriella couldn't seem to unglue herself from the door. One hand was behind her back, still pressed to the door handle, while she nibbled uncertainly on the fingernails of her other hand. Why did she feel so...timid? It wasn't like Troy hadn't been in her room tons of times. But then again, it was the middle of the night...She appraised him, standing in the center of her carpet. She loved that dark-grey V-neck. She had picked it out for him on a mall trip a few weeks ago. It hugged his muscles, showing off every flex of his biceps and every clench of his abs. The thin fabric accentuated the broadness of his shoulders and the strength in his chest. Her mouth practically watered as she gazed at him. And then there were those damn jeans. _Just_ tight enough to spark ones imagination. They hung low on his hips, even lower now, since he had his hands in the pockets. She could just see the waistband of his boxers peeking out. They hugged his butt perfectly and in the front... _Is that a bulge?_ Gabriella's heart stuttered and then picked up double time as she stared at her boyfriend's crotch. She couldn't tell for certain in the dim light, but...

Troy cleared his throat and Gabriella snapped her eyes back to his. _Get a hold of yourself, Gabriella! You're not some silly little teenager...you got into Stanford for Christ's sake!_

Determined to break the awkwardness, she moved forward. "So, um..."

Troy chuckled lightly, his head bowing slightly to maintain eye contact as she moved closer. "Yeah, so..."

"Um..." Gabriella searched for a topic of conversation as she moved about a foot away from him. His Adam's apple bobbed as he swallowed and mischief lit up his eyes.

"Wanna make out?" He suggested. She rolled her eyes as the tension in the room broke.

"Boys. One track mind." She muttered, turning away.

"Hey, I was kidding!" Troy grabbed her hips as she started to move away, pulling her backwards towards him, even closer than before. She could feel the heat of his body through the thin fabric of her teddy. Her heart pounded harder and her pussy began to tingle.

 _God, this fabric is soft._ Troy thought as he gripped Gabriella's hips. She was close enough now that her round, plump behind brushed against the front of his jeans. His cock jumped. He fought hard to control himself as he wrapped his arms comfortingly around his girlfriend. "I would never do anything to make you uncomfortable." He reassured her, embarrassed by his stupid comment.

Gabriella slid one hand over his, which were wrapped around her stomach, and her other hand found her mouth again, a nervous habit. "I know you wouldn't..." She said, leaning her head back against Troy's shoulder. _He is so warm..._ Her eyelids flickered as she drank in his delicious heat. "Not that that would make me uncomfortable."

"Oh?" Troy's interest perked. He might not be able to get _everything_ he wanted tonight, but making out would do just fine. He could always jerk off at home later.

Gabriella blushed, glad Troy couldn't see her face. "Of course not. I love making out with you. You know that."

Troy grinned in excitement and held Gabriella's hips, turning her slowly so she faced him. He slipped his arms around her waist, drawing her closer to him. He wondered if she could feel his hardness. "Well then, shall we?" He leaned his head down, her dark eyes burning into his, but she placed her hands on his chest, stopping him.

"While making out with you, I'm fine with, it's the _other_ thing that makes me a bit uncomfortable."

Troy cocked his head to the side, feigning ignorance. "The other thing?"

Gabriella looked pointedly down towards his crotch, where she could feel the hardness of his dick digging into her lower stomach. To be honest, it turned her on, knowing how horny she made him. She loved knowing that the gorgeous, popular, all-star Troy Bolton wanted _her_. But she had never had sex before. And while she was certain that she wanted her first time to be with Troy, she couldn't help the nervousness that filled her at the thought.

Troy blushed as he watched his girlfriend's eyes flick down to his semi-hard dick, and back up to his face. He sighed. "Sorry...I can't really help that...But like I said, I won't do anything that you don't want me to. I won't even touch you, if that's what you want." To prove his point, even though it was almost physically painful, he stepped away from her, raising his hands in an 'I surrender' pose. She giggled and brought her fingers up to her mouth, gently nibbling. His cock twitched. She had no idea how fucking _sexy_ it was when she did that. Even though the habit meant that she was nervous. He didn't want her to be nervous. He took another reluctant step back. She sighed and crossed to the bed, plopping down on the edge and crossing her legs.

"It's not that I don't want to, Troy." She said quietly, looking down at her own lap.

"Oh?" he encouraged her. He gently kicked off his shoes and slowly moved towards the opposite side of the bed, ready to stop if she told him to, or looked afraid.

"No...I...I _do..._ want to."

Troy froze, at the edge of the bed. His eyes widened. "You do?"

Gabriella rolled her eyes and exhaled sharply, dropping her hand from her mouth. "Come on, Troy, of _course_ I do. Look at you!" Troy tilted his head to the side in surprise before a wide grin split his face. Of course he knew Gabriella had to be attracted to him, but she had never said as much before.

"What about me?" He pressed, hoping she would tell him more. She shifted on the edge of the bed to look at him, annoyance on her face.

"You're...You're _Troy Bolton_."

"Yes, I know my name. But what does that mean?"

She sighed in exasperation. "You're gorgeous, ok? You're hot, you're unbelievably sexy, and anyone with _eyes_ knows that! Even you do! You're just torturing me by making me say it."

He gave a little chuckle, but swallowed it when she glared at him. He sat on his side of the bed and reached for her. She pulled away stubbornly.

"Hey, I'm just teasing you. You've never made any mention of being attracted to be before...I just wanted to hear you say it." Her face softened. "So you were saying? You _want_ to, but...?" He made himself comfortable, lying back on her bed, crossing his feet at the ankles and folding his hands beneath his head.

Gabriella stared at her boyfriend, lounging across her pillows like some kind of Greek Adonis. She wondered for the billionth time what he saw in her. Sharpay Evans and all the cheerleaders were constantly throwing themselves at him. Yet he had been with her _faithfully_ for over a year now...and she wouldn't even sleep with him. She had never out rightly asked, but she knew Troy wasn't a virgin. You just had to look at him, with his cocky swagger, the way he winked at girls in the hall who called out to him, the easy way he slung his arms around her at school...and of course she had heard the rumours in the girl's dressing rooms. How well endowed he was, how amazing his body was, how good in bed he was...Rachel Wood, captain of the cheerleaders had even congratulated her earlier this year, and asked her how she could still walk. Gabriella blushed at the memory. She had made up some excuse to leave at the time. She didn't want anyone to know she was dating Troy Bolton and _not_ fucking him. But she felt bad as she looked at him, patiently waiting for her to speak. He was so much more than gorgeous. He was kind...down to the core. He cared about her...he _loved_ her. He had never pressured her. He had never made her feel frigid, or like a tease. He was content to move at whatever pace she set. She wondered how many nights he had left her place with blue balls. She lay down on the bed too, still about a foot away from him, on her side, her cheek propped on her elbow.

"How many girls have you slept with?" She blurted out, surprising them both. They blushed in harmony.

"Uhh...uh..." Troy looked unsure, for once in his life. Gabriella shook her head suddenly.

"You know what? Never mind. I don't want to know." She became very interested in a particular spot in her bedspread.

"Hey..." His warm fingers found her chin and tilted it up until her brown eyes met his blue ones again. "You're my girlfriend. I have no secrets from you. You're entitled to know...in fact I'm surprised you never asked before. You just caught me off guard, that's all." He tucked a stray strand of hair behind her ear. "Do you want me to tell you?"

She only nodded unable to speak. _Please be single digits, please be single digits._

"Three. I've slept with three girls." Gabriella was surprised to feel relieved. She didn't know what she had been expecting.

Troy's eyes narrowed sardonically. "Well don't look so surprised. I'm not a man-slut, you know."

Gabriella giggled, stretching to place a hand on his chest. "Sorry. I know you aren't."

Troy licked his lips, the amusement fading from his eyes, replaced by seriousness. "I'm still waiting for you to finish your sentence." Gabriella sighed, pulling her hand back.

"I'm scared, Troy. Isn't it obvious? I want to, but I'm scared."

"...ok..." He turned onto his side as well so they were face to face, but still a foot apart. "Physically or Emotionally?"

"What?"

"Are you scared for physical reasons, or emotional reasons? I just want to know what I'm dealing with, here. If you're scared for physical reasons, baby, that's normal. Everyone feels that before their first time. I bet you were scared before the first time you tried riding a bike, too. You just give it a shot. If you like it, you keep going. If not, you try rollerblading instead." Gabriella giggled at his analogy. She loved that he could always make her laugh. "But, if you're scared for emotional reasons...well that's a bit of a bigger deal. If you're scared I'm gonna hurt you, or it won't mean anything to me, or that I'll brag about it to my friends, or, worst of all, that you'll regret it. Well that means you don't trust me, and I hope to God that you do...I mean, you _should._ Have I ever given you a reason not to?"

"No." She answered without a hint of uncertainty. She trusted him beyond a shadow of a doubt. She knew he would never hurt her. And with that, all of her fear evaporated.

Troy smiled at her response. "I love you, Gabs. You are more important to me than anything. I'm not gonna lie, I _want_ to have sex with you...but if you're not ready, I'm more than willing to wait. I can keep on waiting until we're married, it that's what you want. I just wanna be with you."

Her heart melted. She leaned in and pressed her lips to his. He was a tad surprised, but recovered quickly, placing his hand high on her hip, so not to startle her, and kissing back. His dick, which had softened during the conversation, sprang to attention again. Gabriella moved closer, tangling her fingers into his hair. Uncharacteristically, she deepened the kiss, running her tongue against Troy's lower lip until he opened his mouth, granting her entrance. He gave a tiny moan as her fingers tickled his sensitive earlobe and trailed down his neck. She pulled back.

"Troy..."

"Mmm?"

"I'm ready."

He looked at her, appraising. "Are you sure? Don't just say that because you think it's what I want."

"No. It's what _I_ want. I'm sure."

"Really? Cause-"

She groaned in exasperation. "I'm sure! Fuck me already, Wildcat!" His eyes popped wide at her rare use of a curse word and his dick throbbed.

"Well, alrighty then." He half sat up and tugged his shirt over his body, dropping it on the floor behind him before grabbing Gabriella and claiming her lips again. She kissed him back vigorously, his mouth musky and sweet. He rolled slightly, pushing her back onto the bed and hovering slightly over her. He moved his kissed down her jaw line to her neck, which he knew, from past experience, was sensitive. She shuddered and dug her fingers into his back. He gave a tiny moan. He loved the feeling of fingernails down his back, but he didn't say so, afraid to alarm her. He moved his hand down to her ribcage, gripping her soft skin gently. He didn't want to move to fast, but he wanted to feel her chest so badly his palm was tingling. He moved up carefully as he kissed her, his fingers sliding inch by inch up her torso. Finally, he stopped when his fingers met the gentle swell of the bottom of her right breast. He waited there for some sign that this was ok.

She took his hand, bringing it up to her chest. He stared down at her in shock. "Troy, just do what you want to. If you're moving too fast, I'll tell you." He grinned.

"Ok." He squeezed her boob gently and her eyelid fluttered closed. He kissed lower and lower until his lips brushed the soft, warm skin of her breasts. He adjusted himself so that he could grab her other tit as well with his free hand. His cock was so hard it ached. He ground a bit against the bed, hoping to alleviate the discomfort. It wanted to be free.

"Troy?" He looked up at his girlfriend, pausing in his movements. "Can you do something for me?" She looked nervous. He propped himself up higher so that he could look at her.

"Of course. What?"

"I...um...I wanna see you."

"...what?" He looked down at her in confusion. A bright blush colored her cheeks, and she dropped her eyes to his torso. She placed both hands in the middle of his chest and began to run them slowly down.

 _God, his body is incredible._ He was all hard muscles hidden beneath soft, tanned skin. He still had a scattering of freckles from their summer in the sun. His abs jumped as her fingers trailed over them. He swallowed audibly as she tickled the gentle trail of light brown hair that started below his belly button and disappeared beneath his jeans. She tucked her finger into the waistband of his jeans, and he shuddered. She met his eyes again and gave a gentle tug. Comprehension dawned on his face as he realized what she wanted. He smiled, rolled off of her and slid off the bed. She sat up on her knees to watch. He kept his eyes on her as he yanked his socks off, and undid the top button of his jeans. Gabriella's pussy tingled in anticipation. She licked her lips and his eyes darted down to her mouth as he slid the zipper down. He tucked his thumbs into the waistband and pushed his jeans own to the floor, stepping out of them. He wore blue boxer-briefs underneath. Her mouth watered as she took in the sizable bulge straining against the fabric of his underwear. He stuck his thumbs in the waist band of those as well, then looked at her for confirmation that this was what she wanted. She nodded eagerly.

He bit his bottom lip, trying to hide his cocky smile at her excitement, but she didn't even care. He was just so... _hot._ And she wanted to see this legendary cock...she had every right to claim it. No one else was allowed to touch it now.

Still watching her face, Troy slid his boxers down around his hips, and then shoved them to the floor in one swift movement. Gabriella gasped as his cock sprung free.

It _was_ big...somewhere around nine inches in length if she estimated correctly, and she couldn't guess at the thickness, but she hoped she'd be able to get a hand around it. It curved slightly up towards his belly in its hardness, and the pink head was glistening with pre-cum. It looked...delicious. She crawled forwards on the bed, towards him. His cock jumped as she moved closer. She looked up at him. His face was tense with anticipation. She sat back on her heels, gazing at his dick.

"Wow, it's...huge."

He grinned. "Thank you, baby."

"And...kind of _beautiful_ somehow...almost tasty looking..." She clapped a hand over her mouth as she realized what she had just said. Troy laughed at his adorable girlfriend. He was happy she was taking all of this so well.

 _She thinks my cock is 'beautiful'._ "Well, it's yours to taste, anytime you want."

She blushed. He grabbed her chin and lifted so she sat up on her knees and he could kiss her tenderly. She placed her hands on his bare hips to steady herself. The tip of his cock brushed her belly, leaving a spot of wetness she could feel through the flimsy fabric of her teddy. That turned her on so much, she could feel her panties becoming damp. She stared into Troy's burning eyes.

"Can I...?" Her eyes flicked back down to his dick.

"Please." He encouraged, trying to keep the desperation out of his voice. He wanted nothing more in this moment than to see Gaby's tiny hands wrapped around his dick.

She sat back on her heels again, eyeing his dick analytically. She reached out tentatively and touched the head with one finger tip. Troy wanted to groan in frustration, but he bit his lip.

 _She's never seen one before._ He told himself. _Be patient...let her explore._ And explore she did. She swiped up a bead of his pre-cum on her finger and rubbed it between her finger and thumb. Then the slid her fingers gently down the shaft, and back up the underside. His cock ached from her teasing ministrations, but he forced himself to remain silent, and let her play. Finally, she wrapped her entire hand around the middle of the shaft. Troy's eyelids flickered. _Yes..._

"It's so hard...but the skin is so soft...and warm..." Just as suddenly she removed her hard again. This time Troy couldn't stifle his groan. She looked up at him. "What? What did I do?"

" _Nothing, that's the problem!_ " He groaned in exasperation, before he could stop himself. He took a deep breath and forced himself to control his tone before he continued. "Sorry, I just... baby...I know this is your first time, and you've never seen one before, but I swear to God, if you don't touch it, I'm going to spontaneously combust." She cocked her head to the side in adorable confusion.

"Touch it? But I _was_ touching it..." She raised her hand again, gently touching the side of his dick.

"No, like this." He grabbed her hand and wrapped it around his dick. "Squeeze tight." She shifted on the bed.

"I don't want to hurt you." She said nervously.

"You won't. I promise. Please, babe..." She was uncertain, but she wanted to please him. She tightened her grip on his dick. His eyes half closed.

"That's it. You can even go tighter."

"L-like this?" She squeezed his dick and his hips shifted forward in pleasure.

"Yeah...like that. Now move your hand..." He chuckled. "Come on, Gabs, you must know what a hand job is, even if you've never given one..."

Sure, she was familiar with the concept, but she had no idea how one was given. She wasn't about to tell him that, however. She started moving her hand the only way she really could: up and down the shaft of his penis. That seemed to work. He gave a little moan.

"Yeah, like that. Faster, baby...don't be scared." Gaining a bit more confidence, she moved her hand a bit faster, and Troy began to move his hips in time with her hand. "That's it...There you go..." He whispered under his breath. He held her shoulders, his breathing becoming uneven. "Mmm..."

She hoped he was doing well. His moans were sending little electric shocks down to her pussy. He gripped her hips and pulled her up on her knees.

"Don't stop." He instructed and pressed his lips to hers. It was harder at this angle. She scooted forward on her knees until she was on the edge of the bed. She braced her free hand on his shoulder and kept jerking his dick. He moaned as his hands explored her body. With her hand on his dick, he was a lot less tentative as well, and slipped his hands beneath the hem of her teddy to cup her ass. He squeezed her cheeks, giving a little moan in her mouth. One hand stayed on her ass and his other traveled up her abdomen, under the fabric of her top. Her heart beat out of control as his warm hand moved against her skin. He found the bottom of the cup of the top and didn't hesitate to slip hip fingers underneath. Gaby gave a little gasp as he cupped her bare breast. The feeling was amazing. He squeezed eagerly and she reflexively jerked her hand a bit faster on his cock.

With every pump of his hips, the tip of his cock touched her stomach, now exposed as his hand on her chest was pulling up her top. She loved the feeling of the soft, warm tip leaving little wet strokes against her abdomen. She could feel her wetness running down her thigh and she found herself wishing he would touch her pussy.

He trapped her nipple between his second and third fingers and began to roll it back and forth. She broke the kiss to moan, and pressed her face against his neck. He pinched a bit harder and she bit down on his shoulder to keep herself quiet.

Now it was his turn to groan and he shuddered, pressing his dick hard against her stomach.

It was wetter than ever and she gave his dick a hard squeeze.

"Fuck!" Troy pulled his hand out of her top and dropped it to cover hers, stilling her motions on his dick. "Stop...stop."

"Why?" She panted, searching his blue eyes. "What's wrong?"

"Abso-fucking-lutely nothing. You're amazing. A natural." She beamed at his praise.

"Then why do you want me to stop?"

"Because if you don't I'm gonna cum, and I'm not done with you yet." She leaned back, considering that.

"Oh."

"Yeah, oh." She released his rigid dick and he relaxed slightly.

"So...you really think I'm good at this?" He rolled his eyes.

"You know..." He looked pointedly down at his own naked body, and then back at her entirely clothed one. "I'm seeing some incongruities here..."

"Incongruities. Nice."

He winked at her. "Word of the Day calendar. Best birthday present you ever gave me." She leaned in, looping her arms around his shoulder, trapping his dick between their bodies.

"So, Mr. Bolton. What do you propose as the best directive to produce a definitive solution to these...incongruities?" He rolled his eyes.

"I'll give you a directive, Smarty Pants." He leaned down and slipped his hands under her thighs, then pulled her up off the bed. She squealed as he easily lifted her and wrapped her legs around his hips. His cock pressed against her wet panties and she shivered. He turned them around so his back was facing the bed and fell back against the pillows, so she was on top of him. She giggled as they fell, bracing herself against his shoulders. She leaned in, recapturing his lips, and his now free hands cupped her round ass, even rounder as she knelt over him. He squeezed it tightly and gave one cheek a light smack. She wriggled, laughing as she bit his bottom lip.

He couldn't help but smile. He was delighted that she was enjoying herself so much. He gave her ass another smack and she squirmed again, rubbing her crotch against his dick. He ground up against her. _God, she's so wet..._ Her panties were soaked, and clung to her pussy, leaving very little to the imagination.

"Sit up, baby." He whispered. She obeyed, and straightened in his lap, straddling his hips. He licked his lips as he gazed at her, hair wild from their playing, eyes alight with excitement. "Lift your arms up above your head." Again she obeyed immediately, stretching her arms up. He loved how willing she was to trust in him.

He gripped the hem of her teddy and began to pull it up, slowly enough that she could tell what he was about to do, and stop him if she wished. She said nothing, and Troy pulled the garment up, sitting up slightly until her tits bounced out. He yanked it the rest of the way over her head and threw it to the floor. He stared openly at her tits. They were _perfect_. She was about a C-cup, but still on the smaller side, maybe just a full B. Her nipples were round and hard, and practically begged to be sucked. She crossed her arms over her chest sheepishly.

"Hey..." He sat up, and cupped her cheeks. "Don't be embarrassed. You are absolutely gorgeous...every inch of you." He leaned in and gave her a tender kiss. "Still trust me?"

"Of course." She whispered. He circled his fingers around her wrists and gently pulled her arms away from her chest, looping them around his neck instead.

"I love you." He told her seriously, wrapping his arms around her now bare waist. All uncertainty faded from her face.

"I love you too."

"Still want to do this?"

She giggled, and leaned in until her lips brushed his ear. "Abso- _fucking -_ lutely." He grinned at her use of his made up affirmation and kissed her again. He kept his left arm around her waist, holding her firmly in his lap and his right hand found her tit again. Her nipples were even harder now and her breath hitched as he flicked his thumb over her left one. He released her lips and cupped her breast upwards. Again, moving slowly so that she could stop him if he wished, he kissed down her neck to her collarbone, still playing with her nipple. Her breathing was uneven, and her hips moved gently against him. His cock throbbed appreciatively. He kissed down her collarbone and over the swell of her breast and only hesitated a moment before leaning in and capturing her nipple in his mouth. She gasped and tangled her fingers in his hair, holding his head in place. Not that he had planned on moving.

He sucked as much of her tit as he could into his mouth, flicking his tongue over her nipple. She continued to squirm in his lap, her crotch just gently brushing his aching dick. He groaned in exasperation and gripped her hips, forcing her harder against his lap. Her pussy pressed against his dick, and he closed his eyes in ecstasy.

Getting his point, Gabriella began to grind herself against his rigid cock. The feeling of his dick pressed against her wet pussy was incredible. She ground harder. Troy moaned as his other hand found her free breast. He switched his mouth to that one, and flicked his finger over her now wet left nipple. She threw her head back.

"God, that feels good." She hissed, surprising herself.

Troy was so turned on by her words, combined with her pussy grinding against him, that he could no longer wait. He let her nipple fall out of his mouth.

"Yeah? I bet I can make you feel even better..." He whispered, still teasing her nipples with his fingers.

"Oh?" She asked, unable to hide her excitement.

The eagerness in her eyes was all the encouragement he needed. He held her hips firmly with one hand and rolled over until she lay back against the bed, with his between her legs. He spent one more moment, sucking on each of her breasts before he began to move downwards, trailing kisses across her smooth, flat stomach.

Nervousness warred with Gabriella's excitement as he moved lower. She knew where he was going...what he was going to do...she didn't know how to feel. No one had ever even _seen_ that part of her, let alone...

Her muscles jumped as he kissed her lower abdomen, just above the waist line of her panties. She wondered what he was thinking...if he noticed her wetness...it he thought it was weird. He hooked his fingers into the waistband of her panties and a surge of panic went through her. What if she was weird? What if she looked different than other girls...what if she tasted different? What if he didn't like it? A bead of sweat traveled down the back of her neck.

Troy looked up and saw the terror in Gaby's eyes. He paused. "You ok?" She nodded frantically, her face anything but ok. He removed his fingers from her panties. "Hey..I won't do anything you don't want me to do...you know that." She nodded again, but said nothing.

 _Maybe she just needs to get used to me being down here..._ Troy leaned in and laid his head on her inner thigh, his cheek against the wet front of her panties. _God she smells amazing...I want to taste her so badly._ His mouth watered. This was something he had only dreamed about. But he forced himself to be patient. He began drawing little patterns on her opposite thighs, letting his fingers trails across her panties, down through the wet spot in the front and back to her thigh.

 _He's...so patient._ Gabriella thought. _This must be killing him, but he willing to do whatever it takes to make me comfortable._ Her heart swelled with love for her boyfriend. And as her confidence recovered, she began to find pleasure in the gentle trail of his fingers. The brushed right over the top off her pussy, inches from her clit, and she found herself wishing he would touch her there. She reached down and entangled her fingers in his hair. He gazed up at her in adoration. He turned his head and kissed her inner thigh, sending a shiver down her spine. He fingers lingered on her pussy now, slowly travelling down until they found the tiny bump of her clit, swollen and pushing against her panties. He continued raining little kisses down on her thigh as his fingers began tracing tiny circles over her clit. She let her eyes close. It felt amazing. His kisses moved closer and closer to her crotch and he increased the pressure and let his fingers move a little lower. It felt as if her pussy had never been this wet...she wondered if there was a damp spot on the bed below her.

Troy planted a kiss on her pubic bone. "Mmm...I love how wet you are." He whispered. He brought his damp fingers to his mouth and sucked on them.

 _Holy shit, that's hot..._ Gabriella thought.

"You taste so good baby...even better than you smell, which is amazing." He brushed his nose over her panties and she squirmed. His fingers found the waistband of her panties again, and this time she lifted her hips eagerly, anxious to feel his mouth on her. He gave a little grin and sat up slightly to tug her panties down off of her ass and pull them down her legs, until he dropped them over the side of the bed. He made a mental note to take those with him when he left.

Her pussy was unimaginably wet. It glistened, all the way down her ass cheeks. He licked his lips in anticipation. He let his eyes roam over her completely naked body for the first time. _God, she's perfect...I'm the luckiest fucker on earth..._

"You're so beautiful, Gaby." He told her. She smiled and he was pleased to see that all her fear had evaporated. He leaned back down. "Can I taste you?"

She nodded excitedly. Not wasting a moment, he lay on his stomach between her legs, and slid them apart further. He leaned in and gave her wet pussy one long lick. She shuddered and groaned.

 _She tastes incredible._ Unable to help himself, Troy began lapping eagerly at her pussy, slurping up her juices. Gabriella writhed on the bed, gripping handfuls of his hair. He didn't mind. He gripped her hips and shoved his face deeper against her pussy, his tongue finding her little hole and flicking against it.

"Oh my God, Troy!" She gasped. He moaned into her, loving his name on her lips. He turned his body sideways and gripped his dick with his right hand, jacking furiously as his rubbed his tongue against her clit. Her breathing became heavier and she let out tiny adorable squeaks, grinding her pussy against his face. He knew she was getting close. He forced his hand off of his cock and brought his fingers up, rubbing them against her to get them nice and wet before placing the tip of his middle finger against her hole. She pushed eagerly against it and he grinned. Obligingly, he slipped his finger into her. Her back arched off of the bed.

 _Ugh...she's so tight...how am I ever going to fit in here?_ He made little circles with his finger, hoping to loosen her up. She bucked wildly, stifling her cries with her hand over her mouth. He looped his free hand under her thigh and reached up to grab her tit. He rolled her nipple between his finger and thumb and turned his other hand up, so his finger was up against her g-spot. He began to move his finger in and out of her, sucking on her clit.

Gabriella's eyes rolled back in her head. Nothing had ever felt like this before. She felt like she was burning from the inside out. The pressure was building. She knew what an orgasm was, of course but she had never had one before. Nevertheless, she felt like she was getting close to her first one.

As if he somehow knew, Troy slipped a second finger inside of her and flicked his tongue harder on her clit.

"Fuck!" She groaned.

"Mmm, that's right baby, cum in my mouth." As if his words were the key, her orgasm flooded her body like an electric shock. She cried out loudly, unable to help herself. Troy squeezed her tit, his fingers and tongue slowing just slightly, riding the wave of her orgasm until finally she slumped back against the bed.

"Sweet Jesus..." She whispered. Troy laughed, kissing her inner thigh and gently pulling his fingers out of her.

"You know, I don't know where you got such a dirty mouth all of a sudden, but I think I like it." He brought his dripping fingers to his mouth and sucked them clean. Even though she just came, a wave of arousal hit her again.

"W-what does that taste like?" She wondered. He raised an eyebrow in surprise, but then the mischievous light was back in his eyes. He returned his mouth to her pussy, lapping up her cum in his mouth. She squirmed, tangling her fingers in his hair again. Then he crawled up her body until he lay between her legs, hovering over her. He leaned in and pressed his lips to hers, his tongue invading her mouth. She was surprised, but found she didn't mind the taste. She slid her hands down his torso, until they found his still rigid dick. He gave a slight moan as she gripped it. He broke the kiss.

"So...how was your first orgasm?" He kissed her neck.

"Amazing." She grinned, still absently playing with his dick. "But what about you?" He met her eyes, raising a playful eyebrow.

"What about me?" She rolled her eyes and pushed him so he rolled off of her.

"My turn." She moved down his body, not giving herself a moment to think about what she was about to do and become nervous again. She sat back on her heels, her body sideways across his, and gripped his dick. He watched her, not saying a word.

Gabriella took a deep breath and leaned down. She gave his dick an experimental lick. His mouth fell open. Reassured, she opened her mouth and slipped it down over the head of his cock. He hissed, his eyes closing as her tongue flicked the head of his dick.

"Jesus, Gaby..." She took that as a good sign and began sucking on the head the same way he had on her. He seemed to like it. She flicked his tongue over the head again. He squirmed, and his hand gently touched the back of her head. "Move your mouth up and down, like you did with your hand." He instructed quietly. Gaby did her best to obey and slipped as much of his dick as she could into her mouth. Troy groaned, his back arching off the bed. Pleased by his reaction, she moved up and down again.

"Yes baby...suck it." _Suck it? Ok._ She did as he asked, sucking like she had a Popsicle in her mouth. His hand guided her head up and down at the same time. "Fuck...Gabs..." His other hand roamed over his stomach. The hand on her head traveled down her body and around to her abdomen. He slid his hand between her legs and began to gently rub her pussy again. She moaned around his dick and he shivered. He sat up a bit and looped his arm under her body. "C'mere." She was forced to release his dick as he lifted her up and pulled her hips towards his chest. He flipped one of her legs over his body and pulled her back so her crotch was in his face. She was a tad alarmed by this, but had no time to feel uncertain before his tongue was buried in her pussy again.

"Oh God, Troy." She leaned in and captured his dick in her mouth again, bobbing her head up and down and sucking as he had showed her. He moaned against her slit, bringing his hand up and sliding two fingers inside of her again. She ground against his tongue, gripping his dick with her hand. She wished she could fit more of it in her mouth. It was so big, she could only go down halfway before it hit the back of her throat.

As if he could hear her thoughts, he reached down and wrapped his fingers around the hand she had at the base of his cock. He guided her hand up and down in time with her mouth, just like he had done when she was giving him a hand job. Getting the hang of it, she squeezed harder with her hand, pumping his dick as she sucked. Troy's head fell back against the pillows.

"Shhhit!" He groaned. He began to buck his hips up in time with her mouth, making the head of his cock hit the back of her throat. His fingers moved faster insider her and she could feel her wetness running down her thigh. "Mmm...fuck, fuck, fuck...Gaby...I'm gonna cum!" She pulled her head up off of his dick suddenly. He gave a groan of indignation. She looked down through her own legs at him. He gave a tiny chuckle at her awkward position, even as he panted. "Why did you stop?"

"I don't want you to cum yet!" She flipped her leg back from over his head, letting his fingers slip out of her. "This is _my_ first time, remember? I want the whole nine yards." He grinned and pulled her down on top of him so her breasts pushed against his chest.

"The whole nine yards, huh? Is that your way of saying you want me inside you?" She nodded, giving him a wicked grin. He leaned up and kissed her, but then his brow scrunched. "I don't have any condoms with me babe...I didn't exactly expect this tonight." That kind of made her feel even better. She was glad he didn't just walk around with condoms, just in case. "We might have to wait for another day for your first time." She shook her head violently, sitting up on her knees.

"It's ok. I'm on the pill."

"Wait, what?!" He sat up sharply. She rolled her eyes giving his chest a little smack.

"There are reasons a girl goes on birth control, other than for the actual purposes of birth control, ya know."

"...oh." he huffed, mollified. Then he tilted his head in curiosity. Gabriella glared at him.

"Mind your own business."

He raised a playful eyebrow. "Oh, so it's your business how many chicks I've been with, but it's none of my business why my virgin girlfriend is pre-emptively on birth control?"

"'Pre-emptively'. Word of the Day calendar?" He winked. She sighed. "I guess you're right. If you _must_ know, I wanted it to help with my skin, not to mention period cramps and-"

"Gah!" Troy raised a hand to stop her. "Forget I asked." She laughed.

"You wanted to know. And don't be such a child, it's natural. Every woman has a pe-"

"GAH!" He clapped his hand over his mouth. "Please, no more of the P-word." She rolled her eyes.

"Fine." She mumbled against his hand. He dropped it, taking her hand instead. "The point is that we're safe. We can do it, even without a condom." He bit his lip, trying to dampen his excitement. He hated wearing condoms anyway. He was delighted that his first time with the girl he loved would be skin to skin. He grabbed her hips, flipping her across his body and continuing the roll until he was between his legs. Her grin lit up the room. He kissed her forehead.

"Are you sure you want to do this?" She nodded.

"Definitely." He was happy to see her so sure, but he looked into her eyes.

"If you want me to stop, just say so." She nodded again, slower this time, and a hint of hesitation filled her eyes.

"...will it hurt?" She tried to ask as nonchalantly as possible. He tried to answer honestly.

"I don't know, baby. It might. Some girls say it does. Some don't even feel it." She bit her bottom lip, trying hard not to let fear ruin this experience. "Hey. Like I said, if you want me to stop, just say so. I'll be as gentle as I can..." he leaned in and gave her a loving kiss. When he pulled back, she was ready. She slipped her hands around his warm torso, settling them on his hips. He leaned down and sucked her nipple into his mouth. She groaned at the unexpected action. And then his fingers were playing with her pussy again, rubbing lightly against her clit, and teasing her hole. She allowed the pleasure to wash away any uncertainty. He switched to her other tit, dipping one finger inside of her. She pushed her hips against him, already addicted to the feeling of him inside her. He smiled around her breast, loving her eagerness and pumped his finger in and out of her. He could feel the pre-cum dripping from his dick. He couldn't wait any longer. He moved his lips up to her sensitive neck, nibbling gently and removed his fingers from her. He wrapped his hand around his dick, guiding it to her entrance. She stiffened slightly as the tip settled in the depression of her vagina. He paused.

"Ready?" She gazed into his loving eyes.

"Yeah."

"I love you."

"I love you too." He pressed his lips to hers and pushed gently. Gabriella gave an intake of breath as his cock parted her gently. He slid inside her, inch by inch.

 _God, that feels weird...and big._

He moved torturously slow, not wanting to hurt her. A few inches in he met a slight resistance. Gaby winced when he tried to push further.

 _Ok._ He thought. _Like ripping off a Band-Aid._ He moved slowly in and out of her, letting her get used to that feeling. He dropped a hand down and played with her clit again. She moaned. He captured her lips, mid moan and gave a hard thrust. His cock sank in, past the resistance and Gabriella gave a little grunt. He pulled back.

"You ok?" she considered that for a moment, then nodded. He pulled out a bit and she winced slightly. He dropped down to his elbow and sucked on her nipple again, playing with her clit to relax her. He pulled out every trick he knew until she was moaning again. She began to writhe underneath him, moving _herself_ on his dick. _That's it baby..._ He thought. He began to move his hips too, meeting her movements. Slowly he increased the speed of his thrusts. Her breathing got faster.

 _She's so fucking tight!_ Her pussy felt amazing, gripping his dick. It was as if they were made to fit together.

Gabriella tugged at Troy's hips. It felt good...really good. Unlike anything she had ever felt. His cock was creating sensations inside of her that were so delicious she had to bit her lip to keep from screaming. "Harder, Troy. You can go harder."

That was all he needed to hear. He shifted onto his knees more and began to pump his dick harder in and out of his girlfriend. She dragged her nails down his back and he hissed in pleasure. He dropped his head beside hers on the pillow and humped hard and fast, giving in to the feeling.

"God...you feel so good..." He knew he was close to coming. Desperate to hold on for a bit longer, he looped his arm around her waist and rolled onto his back. Gabriella looked unsure as she now straddled his dick. "Come on, baby. Ride my cock." He encouraged. He pushed her up gently, so she sat up in his lap. Her eyes popped wide as she slipped further down on his dick.

" _Fuck_...that feels...well, kinda like your dick is about to pop out of my mouth."

Troy laughed. "I know, this position is deeper. You're in charge. You can control how deep, how fast, everything."

Gabriella smiled. She knew Troy liked to be in control. She appreciated this little gift. She shifted her hips up and then down a bit. His eye lids closed. She sunk a little lower and bit her lip. She felt so...full. But it was good. She moved again, and his dick hit the front wall of her pussy. _Shit..._ that _felt good._ She leaned back a tad and began moving her hips up and down, bracing her hands against his stomach.

"Fuck yes, baby..." Troy murmured. He reached up and squeezed both of her bouncing tits. She moved faster. That spot that his cock was hitting...it felt incredible. She could feel the build of her orgasm again, only this time, much more powerful than before. She slammed her hips down on his dick harder. He began to thrust up to meet her, letting out a stream of curses. One of his hands left her breast and his thumb made small circles on her clit.

"Shit...I'm close..." She gasped. Troy humped up hard into her at her words.

"Fucking cum all over my dick, baby." He groaned, his voice thick with desire. He rubbed her clit harder and squeezed her nipple.

"Fuck!" Gabriella squeezed her eyes tight, her bouncing turning to grinding as her orgasm rocked through her. Troy kept rubbing her clit furiously as she shuddered, gasping on top of him.

Her pussy clamped around his dick so hard, he saw stars. He didn't want to take away from this moment for her, but he need to cum so badly it was almost painful. As her orgasm wound down, he grabbed her and rolled one more time, getting on top of her again. Any semblance of gentleness was lost. The need to fuck her _hard_ took control. He planted both hands on the pillow beside her head and before she could say a word he started to pound into her. She gasped, digging her nails into his back to anchor herself. That only drove him crazier.

"Fuck...drag your nails down my back." He grunted as he thrust into her. She did as he asked, digging her nails in hard and running them all the way down to his ass. "Oh my god, yeah."

Encouraged by his reaction, Gabriella did it again, even harder. He let out a guttural moan and dropped his torso down on top of hers. His hands grasped the wrought iron bars of her headboard as he fucked her even harder and faster. She couldn't stop moaning as his cock slammed into her again and again. She felt like she was going to explode. She dug her nails into his ass, pulling him harder against her. Troy bit her neck, squeezing his eyes shut. The pressure was building in his balls. He knew he was going to cum, and hard. He pressed his forehead to Gabriella's and stared deep into her gorgeous brown eyes. She slid her nails back up along his spine and grasped the sides of his head, kissing him deeply.

"Cum inside me." She whispered, clenching her pussy as hard as she could around his dick. He whimpered as the pressure built up. "Fill me up baby." He slammed into her one more time, so hard that the headboard smack against the wall and he went over the edge.

"FUCK!" He screamed, squeezing her tit with one hand, pressing his mouth against her neck. He kept thrusting into her as jet after jet of cum erupted from his cock, into her body. She moaned right along with him, pulling at his hair. She could feel the streams of his semen inside her body. He had never cum this hard before...it felt so good it almost hurt. He humped hard, shooting with every thrust, his moans turning into cries of desperate pleasure. Finally, it was over, and he slumped on top of her, spent. He body shuddered, his dick unwilling to stop its motion inside of her. His balls ached slightly with the force of his ejaculation.

Gabriella ran her nails very gently down Troy's back and he shivered, whimpering in her ear.

"...holy...fuck...I..." she nodded, knowing exactly what he was trying to say. He managed to lift himself up enough to press his sweaty forehead against hers. She tilted her face up to kiss him. He cupped her face, deepening the kiss. When he pulled away, he shook his head at her in disbelief. "God...Gaby, that was...incredible..." his eyes tightened a bit. "Are you ok?"

"I am so much better than ok." She reassured him, giving him another kiss. He grinned. He shifted and rolled off of her, pulling his softening dick out of her. His eyes widened as he took in the stream of his jizz that poured out of her pussy. "What?" she asked, alarmed by his expression. She sat up and looked down at herself. "Holy shit, Troy!"

He blushed slightly. "Whoops."

"Whoops?" She touched her pussy, now wet for a different reason and her fingers became slick with the creamy substance. "It it always this much?"

"No." He shook his head. " _Never_ that much."

She cocked her head to the side. "Then again, you haven't had sex in over a year." He gave a little chuckle and leaned in to kiss her.

"Well worth the wait. And I'd like to think I bounce back pretty well."

"I'll say." She grinned at him. He smiled, happy she had enjoyed it and rolled off the bed. His legs shook a bit as we walked over to her hamper. He rummaged in it until he found an old towel. He turned back to the bed and froze. Gabriella had scooped up some of his cum and was holding it close to her face, examining it. As he watched, she brought her fingers close to her face and sucked them into her mouth. A wave of arousal hit him so strongly he had to brace himself against the wall to remain upright. His cock jumped obediently, but he was so tired, it didn't get very far.

"Hmm. Tastes pretty good." He bit his bottom lip, crossing over to her.

"That is _so_ hot."

"Yeah?" She gazed up at him, mischief in her eyes. She dipped her fingers back down to her pussy, scooping up more of his creamy cum on her fingers, then licking them clean. He groaned.

"Gabs...stop..."

"Why?"

"Because I can't handle getting horny again...I might explode." She giggled.

"You know, tonight you have gotten me very worried about your potential combustion..." He laughed, and brushed the towel against her pussy, mopping his cum off of her.

"Well, I'll do my best to stay in one piece if it means we'll get to do _that_ again." She squirmed as he cleaned her up and then he did a jump shot, lobbing the towel back into the hamper. She laughed and he settled into the bed beside her, pulling the blankets up around them. She curled into his chest and he wrapped his arms tightly around her.

"Oh, trust me. We _will_ be doing that again." He kissed her forehead as her eyes closed sleepily.

"Yeah?"

She yawned, tucking herself tighter against her boyfriend's warm body.

"Abso-fucking-lutely." She murmured.

And she finally fell asleep.


End file.
